Asymmetric Total Synthesis of Dendrobatid Alkaloids:  Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy

Wrobleski, Aaron D.; Sahasrabudhe, Kiran; Aubé, Jeffrey

doi:10.1021/ja0320018

Cited by 91 publications

(25 citation statements)

References 41 publications

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“…Two NMR features permitted the establishment of the endo or exo configurations of the products: 1) the NMR chemical shifts of the vicinal protons at C2 and C3, which are shielded in the exo isomers, and 2) the coupling constant between these protons, which are larger for the exo products. [11] In summary, we have demonstrated that the MCR for making piperidine scaffolds is considerably expanded in scope compared to the earlier method involving the isolation of 2azadienes. Combining o-nitrobenzaldehyde or N-tosyl-2-indole aldehyde with a transunsaturated ethyl ester led to a high endo selectivity ( Table 2, entries 1-3) and a trans fusion of the two rings.…”

mentioning

confidence: 82%

Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds

Wang¹,

Mena²,

Jnoff³

et al. 2009

Angewandte Chemie

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confidence: 82%

Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds

Wang¹,

Mena²,

Jnoff³

et al. 2009

Angewandte Chemie

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“…Other examples include the synthesis of Vitamin D (10), Artemisinin (potent antimalarial) (11), and 1-monoesters of 2-ketoalkanedioic acids (12). Ozonolysis is also a key synthetic step in the formation of Indolizidine 251F (13), which is a potent alkaloid naturally found in poisonous frogs skin.…”

Section: Ozonolysis Advantages and Applicationsmentioning

confidence: 99%

A New Paradigm in Oxidative Cleavage Reaction: The Use of Continuous Reactors To Enable Safe Scale Up of Ozonolysis

Allian

2014

ACS Symposium Series

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“…Following the pioneering work on the synthesis of [x.3.0] bicyclic systems by RRM from norbornene derivatives [35], Aubé et al applied this strategy to synthesize indolizidine alkaloid 251F, where enone 76 was obtained from the rearrangement of norbornene 75 (Scheme 11.20) [36]. Early attempts afforded the desired product in only poor yield (30%) mainly because of olefin oligomerization.…”

Section: Synthesis Of Indolizidine 251f (±)-Trans-lumausyne and Aburmentioning

confidence: 99%

Cascade Metathesis in Natural Product Synthesis

Porta

Blechert

2010

Metathesis in Natural Product Synthesis

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IntroductionAlkene metathesis is well established as a valuable synthetic tool in organic chemistry, and has proven to be a unique technique for the construction of complex structures in a rapid and effective way [1]. Since all metathesis transformations (except diyne metathesis) can be promoted by the same carbene catalysts, it is possible to combine them in a sequential way and enable a metathesis cascade in one pot. A domino reaction has been defined as ''a process involving two or more bond-forming transformations which take place under the same reaction conditions without additional reagents and catalysts, and in which the subsequent reactions result as a consequence of the functionality formed in the previous step'' [2]. These domino processes, also called tandem, provide a tremendous increase in molecular complexity within the use of one single catalyst in one pot. By carefully adjusting the conditions and judicious choice of the catalytic complex, it is often possible to conduct the process with excellent regio-, chemo-, diastereo-, and even enantioselectivity. Domino processes are especially attractive not only because they provide elegance to the synthetic route but also for being ecologically and economically favorable since they minimize the amount of waste, solvents, reagents, and energy compared to stepwise reactions. Much effort has been invested in developing new methodologies involving metathesis domino processes that have been successfully applied to the preparation of biologically active and naturally occurring molecules. In this chapter, a selection of synthetic approaches with ruthenium-catalyzed domino reactions that include exclusively metathesis steps will be discussed, whereby syntheses involving tandem reactions connecting a metathesis reaction with a reaction of a different type [3] or several metathesis transformations occurring independently at the same time will not be described [4]. Through this collection of natural product syntheses, we would like to highlight the high efficiency and utility of metathesis domino reactions in organic synthesis, discuss its driving forces, limits, and scope, and ultimately illustrate the enormous synthetic potential of this transformation.

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Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl Analogue Using an Intramolecular Schmidt Reaction Strategy

Cited by 91 publications

References 41 publications

Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds

Multicomponent Reactions for the Synthesis of Complex Piperidine Scaffolds

A New Paradigm in Oxidative Cleavage Reaction: The Use of Continuous Reactors To Enable Safe Scale Up of Ozonolysis

Cascade Metathesis in Natural Product Synthesis

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